My Sisters Pt. 03: Jill

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Mar 31, 2021 // By:analsex // No Comment

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Jill’s house stood in a large garden in a leafy part of town. Jill had her own business, and at 24 she was considered a bright young thing in the business world. Great things were expected of her, and as far as I knew, it was so far so good. She had a lovely big house, brought with the proceeds of her manufacturing companies. She did something in steel and something in fibre glass and something in lingerie — an odd mix but she seemed on top of it all. She wasn’t married and as far as I know had never had a serious relationship. This was a concern for The Parents, apparently, they went on about it all the time. What is it with Parents and daughters? They never hassled me about my unmarried and childless state, so why put all that on Jill? She seemed happy enough, although her relationship with The Parents had become rather tetchy of late.

To be honest my relationship with Jill was not the best either. Despite being her stupendously gorgeous and talented brother Jill never made any effort to contact me, or showed any desire to spend time with me. She was the youngest of the sisters, and therefore closest in age to me, but that didn’t seem to count for much. I’m not saying we didn’t get on or we have fallen out or anything like that, just that we don’t have the easy communication I have with Claire and Beth. As I swept down the long gravelled driveway towards Jill’s house I wondered how I was going to complete my plan….. fucking one sister, problematic. Fucking two sisters, a miracle. Fucking three sisters, an impossible ask? Especially when the third sister is likely to be the most resistant to even the suggestion of a brotherly fuck.

As I always do I parked my car around the back of her house, next to the kitchen. Jill said she would be home around two, so it was no surprise to see her red sports car parked there too. I pulled up next to it, climbed out of my car, and went through the gate towards the back door. I was feeling nervous! Me, Mr Confidence himself. My cock was unusually quiet…..nothing was stirring down there. Not a good sign, although not an unexpected one in the circumstances. As I approached the door I began to wonder how this day would end. Would I fulfil my mission, or end up in frustration in more ways than one? What if Jill did not want to….do it? It would be pointless offering her a cut of the money, she had more than enough of that already. Money, or at least a little bit extra, would mean next to nothing to her. Even the whole lot would barely turn her head. Would I have time to find another woman? I could buy one easily enough, but that would be against the rules. Nope, I’d just have to do my best, use my whole arsenal of winning charms, and hope against hope that my sister would relent and let me fuck her. Just the once. No long term commitment, just in, out, shoot my load, one million dollars thank you very much. Surely a sister would indulge her little brother, just the once?

The back door was open, so I went through and into the house. Jill was there, in the lounge room, standing looking about her. She looked at me over the rim of her glasses.

“Hello Dan,” she said. I smiled and gave her a little wave. “Samples,” she said, opening her arms and indicating around her. On all available surfaces were sets of underwear, knickers, bras, camisoles, slips, corsets, all colours and patterns and styles. “Summer collection time again, I’ve got to choose.” She looked at me as I stood there. “Coffee?” she said.

Jill is a very pretty, happy looking woman. She has similar features to the other two but she just carries it off in a more, I don’t know, sexy and feminine way. She has a natural confidence about her, verging on arrogance, but she has the sweetest smile which disarms and invites at the same time. Men and women go weak at the limbs in her presence which is not a good career move for them because she is quite ruthless in her business dealings, and she will exploit any weakness to her own advantage. Drooling men are putty in her hands. Whimpering women seeking her approval have no chance. I am somewhat impervious to her charms, and usually it really doesn’t matter to me, but on this occasion I had a mission and a purpose and my task was to break through that force field and get my cock into her knickers.

“Do you have anything stronger?” I asked. “Beer?”

She looked at me. “Of course,” she said. “Hard day at the office?” She smiled.

Now, that got me wondering. Her magic was working on me already! Did she know anything? Had Claire or Bethany talked to her? Was this just chit-chat, or was she maneuvering for position? She was so good at finding a chink, which she would then unceremoniously drive a bus through.

She opened the fridge and took out a beer, which she waved at me. I shrugged and nodded.

“Claire called,” she said, slipping her finger under the ring-pull of the can. As she looked at me, she ripped the ring off with a pssst, and handed me the can.

“Glass?” she said.

“Did she?” I said, shaking my head at the offer of the glass. I took a pull from the can. Ah, şişli üniversiteli escort lovely and cold, just what I needed. Too cold to taste, but that’s the only way to drink that sort of beer.

“She did,” said Jill. She pointed to a chair and slipped herself onto one in one elegant movement. Jill was wearing a lovely tight fitting dress, typical of the sort of clothes she wore. It hugged her beautiful figure without being suggestive, and displayed just the right amount of cleavage to leave you in no doubt that this was a woman in full control of herself, and a strong, assertive woman, do or say anything about her body at your peril! The dress was black, and it had flecks of white and red and other colours all over it as if a painter had loaded his brush and flicked the material from afar. It was lovely. And when she lifted her arm to play with her hair I could see under it, which revealed she was wearing a deep red-coloured lacy bra. Again, suggestive without being slutty, and definitely a challenge to the viewer to know what to do with that information. In the right hands that is powerful stuff indeed, and Jill’s hands were crafted from the right stuff!

“It seems,” she said, “that you have caused quite a, what shall we say, stir…amongst the sisters?” She took a sip from the glass of water she had poured herself. She kept her eyes on me as she did so. I took a swig from the beer.

“It would seem so,” I said slowly, my eyes not moving from hers. “Stir is probably a good word,” I said.

“Hmm,” she said, slowly putting her glass down. She raised her arm and pulled a strand of hair back behind her ear. “Claire was……” she started, then she stopped and quietly drummed her finger nails on the wooden table top. “Claire was……Claire was remarkably….obliging, wasn’t she?” She smiled, but her eyes didn’t smile with her lips.

“Obliging?” I said. “Sounds rather….contractual. I’d have said more like…involved.” I smiled back. “Enthusiastic, even.”

“Hmm,” said Jill. “Claire is never enthusiastic, she’s too….cautious.”

“Not this time,” I said. “Guarded yet deliberate, I’d say.” I took another drink from the beer, which drained the can, so I scrunched it up in my hand and placed it, in a tight ball, on the table. Jill watched me in silence.

“Bethy, on the other hand,” she said, “sounded quite overcome.” I smiled at her choice of words.

“You could say that,” I said.

Jill looked at me for what seemed like a long time. Then she stood up, went to the fridge, took out another beer, pulled the ring top off and threw it into the sink, and then returned to her seat, sliding the can across the table with a perfect weighted push which had the can sliding to a stop an inch from my hand.

“When a potential client wants to do a deal with me, I expect them to do a great sales pitch,” she said, smiling again. That smile of the assassin. She raised her eyebrows.

I looked at her for a moment. Then I put the can down on the table with a thump. I stood up.

“Fuck it, Jill. I’m not playing your fucking game,” I said. She sat back and folded her arms. “I need to fuck you to win one million dollars from Thomas, I know that’s, well that’s, it’s well, it’s what it is, I know that’s not a lot of money to you but it’s the whole world to me and I’ve….done two thirds of the task and as bizarre as this may sound I’m asking you to let me fuck you in the traditional way, nothing weird, just a normal….” I shook my head, ” a normal boy-girl thing, boy-girl fuck, you know, missionary and all that, just the once, you can shut your eyes and wear a head set playing any music you like, or radio, radio’s fine too, and once it’s done we can just forget about it and go back to normal, maybe we can’t but we might be able to just forget it ever happened and I can get the money and you can, well, you can be happy you helped me get ahead. You’re good at that, Jill, it’s an endearing quality you have. Amongst lots of other endearing qualities.” There was silence. I couldn’t cope with silence, I needed noise. “Claire quite enjoyed it actually. So did Beth.”

I stopped. Jill sat for a moment, arms crossed, looking at me intently.

“Isn’t there a photograph involved?” she said.

“Two. Before and after,” I said.

More silence. Then Jill uncrossed her arms, quietly stood up, and walked towards the door.

“No,” was all she said as she left the kitchen.

I sat for a moment. Then she put her head round the kitchen door.

“Absolutely not,” she said, then disappeared again. I sat.

She appeared again.

“Under any circumstances,” she said. She disappeared. Then reappeared.

“How could you even ask?” she said, disappearing before an answer could be given. A moment passed. Then another. I stood up. She reappeared. She walked into the kitchen fully, and stood, hands on hips, looking at me. She was shaking her head.

“Jill?” I said.

“No. No. No.” I made to speak but she put her finger in the air and waggled it at me. taksim anal yapan escort “No!” she said, and left the room.

This was not a good turn of events. Jill was usually a one-no woman, just as she was a one-goodbye person on the phone. Some people say goodbye three or four times at the end of a telephone call before they put the phone down, with Jill it was always just the once. And before you could say anything, or do anything, she’d have hung up and you’d be left with the dial tone. It always felt a bit rude to me, but Jill felt that one goodbye was quite sufficient.

And one no.

I had had six, plus an ‘absolutely’ and a ‘how could you ask?’ which was equivalent to half a dozen nos. I had a sinking feeling at the pit of my stomach, and deep inside my bowels. My sphincter contracted. I could see the money just floating around in the sky, just out of reach of my grasping hands. Perhaps the whole thing had been a colossal mistake from the beginning?

But this day the gods were smiling on me, and before even a minute had passed a solution to my dilemma presented itself at the front door. The Parents.

Jill was surprisingly nice to me.

“Oh God, it’s the Parents. If you don’t want to get dragged into an afternoon of hell, go and hide.”

“Hide!” I said. “Why?”

“They’ve come to tell me I should get married, no doubt, like they always do when they come round unannounced. I hate it! You don’t want to get involved, trust me.”

“No,” I said. “Where should I hide?”

Jill looked at me for a moment. “Anywhere upstairs. There’s a loo down here so they shouldn’t need to go upstairs at all, so you’re pretty safe.” She smiled at me, then lay her hand on my arm. “My pretty brother,” she said.

It didn’t take long to kick off. I could hear the shouting from upstairs. I went into Jill’s bedroom and sat on the bed. Was this the end of my scheme? End of my plans? Was Thomas going to be proved to be right, that I couldn’t fuck three women in the one day?

I heard footsteps coming up the stairs. Stomping footsteps, angry footsteps. Jill came into the room.

“Fucking hell!” she said, almost in a hiss. She was carrying all the items of lingerie in her arms, and she threw them onto the bed.

“Nothing I do is right for them! Nothing!” She slumped down next to me. I put my hand on her leg. She looked up. I put my arm around her shoulder, and gave her a hug.

“Hey,” I said. “Ignore them.”

She sat up, then stood up.

“Fuck them,” she said. She was seething. Then she looked at me, and a little smile came to her lips. Then the smile grew bigger, and bigger.

“What?” I said.

Jill took one step towards me, then slowly lowered herself until she was on her knees. She put a hand on each of my legs, and slowly pushed them apart.

“Put your cock in my mouth, brother,” she said, smiling hugely. She had a twinkle in her eye. I tried to say something, but no words came to mind.

She reached forward and put her hand on my crotch.

“If they are going to fuck me over, you might as well too,” she said. She was still smiling.

It’s funny how the mind works sometimes. There I was, being propositioned by my sister, being offered sex with her, for whatever bizarre reason it matters not, but being offered what I had really assumed would never happen, yet all I could think at that moment was ‘it’s the wrong fuck.’ The wrong fuck! I’d already had Claire in the mouth, and Bethany in the ass, I needed to have Jill in the cunt to win my money, but she was offering her mouth, so it was the wrong fuck! And because my mind told me that, it refused to send the right message to my cock, which remained resolutely limp.

Jill squeezed me. The smile on her face remained.

“Get him out, Dan. Sisters told me he was a specimen, I need to find out for myself.”

So I slowly stood up. Jill sat back on her heels as I unfastened my belt, and she watched as I unzipped myself and let my jeans fall to the floor. I stood there in my boxers, spectacularly unready for action. She reached up and slowly eased my boxers down. My cock didn’t exactly leap out at her, more like flopped out and lay there, disinterested.

Jill shook her head, still smiling.

“Let’s see what I can do about that,” she said, and without further ado she leant forward and took my cock into her mouth. She slid it in and with a gentle suck took it right in, the whole shaft. Wow! The feeling of warmth and wet was astonishing, and Jill started a little humming sound which vibrated through her mouth, and on through my cock. It responded. Jill started sucking gently, not using her tongue yet, just her whole mouth, then she started rocking gently back and forwards, letting my cock in then out, in then out.

I looked down. She had her eyes closed, and she looked beautiful. She looked especially beautiful with her mouth wrapped around my cock, and as the rocking movement grew faster, my cock became harder and harder and bigger and bigger. It no time taksim bdsm escort it was full and throbbing and Jill’s mouth had extended to take it all in. Then with a long slow pull Jill let my cock out of her mouth and she sat back on her heels to inspect it. She was panting.

“The sisters were right!” she said.

Then there was another voice. Mother. “Jill. Jilly! Are you up there?”

Jill looked up at me, and smiled.

“Just coming, Mum,” she called, wrapping her hand around my cock. “Won’t be a sec.” Then she spoke to me.

“You’ve got one minute to cum, brother. I want it long and big and all in my mouth. Go!” And with that she opened her mouth and slid my cock back in. This time she was like a wild thing, using her tongue and her lips, slipping my cock in and out, licking the shaft, the head, nibbling the underside while licking at the same time — how did she do that? — her hand was pulling at my balls, tickling, scratching, the feeling was intense as I felt my orgasm building, my sister knew how to handle a cock, that was for sure, I started pumping, back and forwards, she started humming again, only louder this time, the hum vibrated all along and through my engorged cock, it was wonderful, Jill’s head was pumping back and forwards, I grabbed her hair and pulled her in then pushed her back, she didn’t resist, just went with it and gave me strong, hard sucks between soft gentle ones, then there it was, the feeling, the urgency mounting in my anus, that moment of ecstasy when you get to the brink and this time, this time, you fall over it, there’s nothing you can do, you fall over the precipice and you need to push it all out and cum and cum and cum, wave after wave of excruciating delight. I came in my sister’s mouth, I held her head still and pumped my orgasm into her, she knew what to do, she stopped sucking and licking and just let me flood her, fill her mouth, she let me pour myself into her, with her eyes closed and her mouth open, her mouth the perfect O for my cock, the perfect receptacle, and I obliged. I fucked her mouth and kept fucking it until I had no more cum to give her.

Jill sat back and slipped my cock out of her mouth. She licked the last remaining drops of cum from my shaft, inspected it to make sure I was completely clean, then she licked her own lips, and smiled. I looked down at her. There was not a drop of cum on her clothes.

“Hmm,” she said. “Sisters were right.”

Then without a moment’s hesitation, she stood up, went to her dressing table and looked at herself in the mirror. She brushed at her dress, ran her hand over her breasts, and smiled at herself. “Lovely,” she said.

“How did you do that?” I said, sitting back on the bed. “You swallowed it all?”

Jill strode across the room, almost bouncily, and headed for the door.

“Now, the Parents!” she said. “I feel really quite saucy.” And she disappeared.

I was left alone. What an incredible orgasm! And my sisters…..well, I knew they were amazing, but they had shown another side to them today. Not something brothers usually discover, I suppose, or maybe all sisters are like that?

I lay back on the bed, and covered myself with Jill’s lingerie collection. The one thing I miss about not being into women is the lingerie thing, it is just so sexy. Men have their own stuff but it’s not the same. Women’s underwear is somehow at another level entirely, any straight man who doesn’t indulge him and herself in it is a fool. I suddenly felt tired. It was past four o’clock in the afternoon and I had been quite busy today. I felt myself fading, drifting off to sleep. I let myself go with it.

I awoke with a start. Something had jolted me awake. I opened my eyes. All I could see was material. Black, speckled material. But then, as my eyes grew accustomed to the light, I could make out something white, and something not quite white, and then the white receded and the black came back into focus. I blinked, and wiped my sleepy eyes. I looked up. It was Jill. She was standing on the bed, legs either side of my body, and I was looking straight up her dress. The white was a small triangle of white knickers between her legs. She was standing above me holding her dress up. She was smiling.

“You have ten minutes to fuck my ass, brother. Father has gone to buy some cakes, Mother is making tea and sandwiches, and I told them I needed fifteen minutes for a little cat nap. But….” and she raised one foot and placed it on my sleepy cock, pushing me with the short heel of her shoe, “I want brother cock in my ass, like Bethany got. You up to it?”

Oh dear! Another wrong fuck! But we were heading in the right direction, so I nodded.

Jill pulled up her dress and slipped her fingers into the band of her knickers. She smiled as she slowly pulled them down her long, slim legs. I got the first glimpse of her pussy, tended but not shaved completely. It had a nice edging of hair around the lips. Another beautiful pussy from another beautiful sister! Jill lowered the knickers until she got to her knees, where she wiggled her legs and let the knickers fall. She bent and collected them, held them aloft, then dropped them onto my face. White lacy knickers. I inhaled and could just make out a scent. My cock was stirring. Even though I had long ago shifted my interests away from pussy, there was something about the raw smell of a person that always excited the body parts.

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